Mentoring Effectively — The Nitty Gritty

In one of my past roles, I witnessed an executive leading a project with another business unit leader, “project lead”. The project started off with the executive painting the picture for the end goal and describing it to the business unit leader. This project lead went ahead and attempted to tackle the assignment. When it came time to reveal the findings, the results were not up to par with the executive’s standards. Then during a leadership meeting, the executive mentioned, “the people I am mentoring are not learning, so I end up doing it all myself” and “I do not have enough time to train people.” This executive is not an effective mentor.

Mentoring takes patience and intentional effort. The following post will walk through step-by-step on how to be an effective mentor.

To help navigate your reading, the following sections were utilized:
I. Purpose
II. Background
III. Approach
IV. Closing Remarks

I. Purpose

In the past, there have been other posts about mentoring, primarily about traits mentors have or some general principals to follow. Mentoring is a great way to develop team members, but is not always effective. This article will provide a detailed view into effective mentoring, which optimizes both mentee growth and business results.

For the purposes of this article, mentoring will signify a senior colleague, typically a manager, developing a more junior team member on how to become a better problem solver. Mentee growth is expected to arise from receiving targeted projects and proper feedback along the way. To further clarify our subject, there are other aspects of mentoring (e.g., social, emotional) that will not be discussed. The “you” mentioned throughout the article refers to the individual looking to become a more effective mentor.

II. Background

As a boss, work can be done by you or by your teammates. If you are distributing work to your teammates, there are three different cascading methods. To help explain these, let’s assume our new project is to build a house:

• Micromanaging: Boss gives very explicit directions: floor plan, materials to use, process flow, timelines, etc. Team members, construction workers, execute the plan.
• Mentoring: Boss gives a general idea with some necessary parameters defined: size of the lot, budget, timeline. Mentee comes up with approach and regularly checks-in. Boss gives feedback to help the Mentee think further and thereby become a better project manager, or in more general cases, a better problem solver.
• Empowering: Boss tells a leader, “I want you to take the lead for this housing project.” Leader, architecture firm, owns the process. Boss and leader check-in sparingly.

Typically, a boss should not and cannot rely on an individual method. There are some cases where micromanaging will be more effective and others where empowering are more effective. The basis for which method to choose depends on your talent pool and project specifications. Focusing first on the talent pool, if your team has not been trained, you will likely need to micromanage more. Therefore if you do not invest in training or hiring capable leaders, you will likely micromanage forever. Empowering is an efficient option for the boss and the leader, but a boss can only empower if capable talent exists on the team. Now referring to project specifications, if the task is very simple, micromanagement may be the easier option. If the project is more complex, empowerment would be preferred.

Mentoring sits in the middle and is a long term play. Investing in mentoring will develop capable mentees such that one day, you may be able to empower them. Expect articles on “Empowering” and “Micromanaging” to come later.

III. Approach

To mentor effectively, we must invest time and effort into the three following steps: 1) Mentee selection, 2) Project fitting [to the mentee], and 3) Feedback cycles.

Mentee Selection

Imagine that you are on a racetrack and need to select your vehicle. Some cars have high drive, but cannot turn well. Some cars can turn well, but have low drive. Some cars are bad at both. Some cars have high drive and also turn well. Needless to say having the vehicle that is strong in both traits would be optimal.

Selecting a mentee is like selecting a race car. You want to choose the ones with high drive, ambition, and ability to turn, learn. As mentioned previously, mentoring requires time investment. Investing in a mentee with high ambition and high ability to learn will increase your chances of making it around the track a few times, successfully completing projects. For a visual representation, see the figure below.

As suggested, let us focus on the top right quadrant for now. I will discuss the other quadrants in future posts. After understanding the structure, we need to be able to place our team members into one of the three categories by testing their ability to learn and level of ambition.

• Ability to Learn: I want to separate ability to learn from baseline capabilities. For example, someone can be a high performer in one area, but has not shown the ability to excel in new tasks. Alternatively, someone can have no experience in one area, but demonstrate ability to excel in new tasks. So to test ability to learn, underhand toss them a few new ‘trial projects’ (i.e., not part of their daily routine), along with some basic fundamental training if necessary. Then, you can gauge if and how the individual is able to solve the problem. If they excel, and have built your trust in them, place them in the high ability to learn category.
• Level of Ambition: Let us define ambition as the burning desire to learn more. We can test this by checking in on our direct reports. My preferred channel is one on one coffee chats. During these chats, I ask what are their personal goals for the next 6–12 months. If the goal is large, I’ll help break it down to smaller tasks and skills that we can work on learning. If there is no large personal goal, I’ll ask what do they want to learn? If they mention that they are not interested in learning, I’ll place them in the low ambition category on my internal board.

Note that it is possible for your team members to shift from one quadrant to another over time — perhaps they find inspiration down the line or demonstrate they do have a high ability to learn. If no one on your team is in the top right quadrant initially, focus on the motivating individuals who have a proven high ability to learn, but do not have high enough ambition yet. For any remaining team members, focus on micromanaging, not mentoring, them. Do not spend time teaching individuals who cannot learn. Conversely, you may have multiple ambitious fast learners, in which case, you can certainly mentor multiple at once — pending project availability.

Project Fitting

Remember one of our key goals is to optimize for employee growth. After selecting our mentee(s), we need to determine what projects would be a good fit for them — ones that stimulate the mentee in areas they want to grow. The project would likely be additional work beyond their regular scope. Choosing a project that fills in desired skill gaps for the team member is critical because the “additional work”, will feel less taxing compared to assigning a project that teaches irrelevant skills to the mentee.

If the mentee is interested in something outside your scope, see if there are skills, both hard and soft, you can help the mentee build to get there. If your projects cannot help them build towards their goals, see if there are relevant cross functional projects to get person involved in. To further illustrate these ideas, let’s discuss a few different fictitious mentees, their goals, and potential projects we can assign them.

The project areas should be broad objectives in order to give the Mentee more freedom to make decisions and thereby get closer towards their ambitions.

After narrowing down potential projects that would help the team member get close to their personal development goals, we still need to further refine the project scope. Earlier, I mentioned the other goal from mentoring is to drive business results. So, we need to select a project that has impact, but also provides enough time for the employee to learn and make mistakes. The following diagram can help us visualize how to select projects:

We should only be assigning high impact projects or those that provide a meaningful result. Next, we are targeting projects that are not urgent, which will provide enough time to run through iterations or feedback cycles. Urgent is relative in every business, but for our purposes, we will say urgent means there is just enough or not enough time for a fully trained team member to complete the task. Let us define not urgent as anything more than just enough time. Since the mentee is not fully trained in this target area, we need to give them not urgent tasks. The ‘trial projects’ can be used to gauge the readiness of mentees, as mentioned in ability to learn section above. If you have a mentee, but cannot find a matching project, consider ideating high impact strategies more or breaking up an existing project.

After selecting a project that fits the mentee, we will need to explain a minimum of two things 1) overarching goal and 2) deadline. Beyond these two things are additional details, which I’ll call handholds. In the beginning, more handholds will help the mentee get started. Over time, you should provide fewer and fewer handholds.

In the context of our house building project, some handholds might be:

• “Consider how the windows should be set up to optimize for natural sunlight”
• “There may be issues with setting up sewage pipes here. Make sure to take these into consideration in your plan”

This project explanation step is crucial to project fitting since the foundation (goal, timeline) has been provided, but the floor plan (specific direction) HAS NOT. For the first few projects, feel free to provide more handholds to the mentee, but start to taper them down over time. You may wrap up the project explanation with any questions the mentee may have and agree upon a time to check on the approach before starting any actual work. Then, you can send them off to develop their own approach.

Feedback Cycles

After they received the project explanation from you, we can start the feedback cycles (see figure below), which will be the main learning mechanism for you to guide the mentee.

As the mentor, you decide whether the project is complete or needs another review cycle. The number of cycles will vary by project complexity and mentee experience. For more complex projects, you should look to check in more frequently. Complex in this situation should refer to the number of novel decisions the mentee needs to make. Similarly, for less experienced mentees, you should also look to check in more often, to ensure they are headed down the right path.

In every case, the first feedback cycle should happen after they have developed an approach. The approach may vary from one field to another, but see below for some samples from the mentees mentioned earlier.

After reviewing the approach, if you approve, you can let the mentee proceed. If you do not approve, you can either provide specific recommended edits or parameters to consider exploring. Providing specific recommended edits will help save time, but will give the mentee less room to stretch their own thought processes. Giving parameters to consider exploring or asking targeted questions, will force the mentee to spend more time thinking. As much as possible, I recommend giving the mentee parameters to consider to stretch them further. If the project is running behind schedule, you can provide specific recommendations. To help understand the differences between specific recommendations and parameters to consider, refer to the following table:

Remember, the primary goal of mentoring is to optimize for the mentee’s growth. Through asking questions, we won’t give them the approach. Instead, we will guide them to think about the approach on their own. Also for those who are not familiar with Chemistry, distillation is typically used to increase the concentration of a substance.

Post approach alignment, we need to establish the cadence for future meetings. Typically, it should be before the next major decision or as soon as the mentee is not certain about the best next step (i.e., “gets stuck”). If the milestone has not been met, but the scheduled date to meet has arrived, I would recommend still meeting to discuss hurdles and inefficiencies. In addition to setting a formal time for review, the mentor should also have an open door to answer any small questions between feedback sessions.

Both the Mentee and Mentor should prepare before the feedback session. To ensure the Mentee shows up prepared to each review session, have them share status updates and relevant materials created so you can review beforehand. If they are able to send materials beforehand, and you are able to review beforehand, more time can be spent thinking about problem areas and next steps as opposed to reviewing existing work. To ensure you are prepared before the actual meeting, on top of reviewing their work thus far, spend time forming an opinion on the direction and next steps. We want avoid becoming a “Lazy Mentor”, a mentor who doesn’t think about potential approaches beforehand and just relies on the mentee to do all of the thinking and executing. As mentor you do not need to know all details and possibilities, but you do need to spend time thinking about logical approaches and potential problem areas.

Each feedback session should start by discussing updates thus far and end with next steps. Treat each review session as a brainstorming session, where your job is to moderate. Allow them to express their ideas and keep your opinion flexible, meaning if the mentee has a better approach, you should support their path. However, if you see improvement points or if they are not sure about next steps, we will need to ask the right questions such that the Mentee can come up with the idea without you giving it to them directly. This follows the same train of thought as “giving parameters to consider” or “asking targeted questions” mentioned earlier.

Hopefully through your line of questioning, they have come up with many new ideas to get over their roadblocks. Now ask them to prioritize the new ideas. If their prioritization seems inefficient or inappropriate, explain what they should be considering when prioritizing so and have them correct it. Put in another way, we are not telling how to prioritize, we are telling how to think about prioritizing.

Post approach alignment, the feedback cycles will continue until the project is completed. As you invest more time, and provide more feedback in the form of thought provoking questions, you should see the mentee continue to grow and develop.

IV. Closing Remarks

We mentor because we want to improve the problem solving capabilities of our team members, both for their personal development and project completion. To do so, we need select ambitious, fast-learning mentees, fit a project that builds towards their goals, and provide regular feedback that stretches them even further. After a Mentee gets enough repetitions and learns to problem solve, they will soon be able to take bigger projects — independently tackling those high impact and high urgency projects. Then, you can begin solving more problems and/or start developing additional team members.

Are there nuances that I missed? If you have any comments or questions, feel free to respond below or connect with me on LinkedIn. Please follow me on medium.com/@dhuynh2979 for more articles about leadership and management.

I would like to thank my own mentors for everything they have taught me — Jeff Lu, Vang Xiong, Brendan Speechley, Margaret Lee, and Timothy Reyes.